Microsoft vs Google: clash of the titans

A question that comes up fairly regularly in the small business world is how to handle email. Most companies start out with a simple POP account, or maybe even a free address from Google, Yahoo, or MSN. It’s an easy way to get started, but at some point you need more – integration with smart phones, shared calendars, links with company software, better security, and more.

Many companies are opting for Google Apps over Microsoft Exchange. It can be a good option in the right circumstances, and in fact we used Google Apps ourselves for over a year. The web portal is easy to use, the search is lightening fast, and I still miss the unique way Google organizes conversations. Google’s built-in spam filtering is excellent, and because they operate “in the cloud,” they manage the servers so you don’t have to. The downside is that if you have trouble, you are dependent on them for support. If you use a free account, good luck – it may take a while.

Microsoft Exchange is still the powerhouse in the email game, and the level of sophistication is hard to beat. It will take more technical skill to maintain your own in-house Exchange server, but if you take that on, you have far more options available to you. You can set security nearly any way you like, you can track down deliverability issues (generally difficult or impossible with a hosted solution), and most software packages that require email and calendar integration work with Exchange by default. Use a spam filtering service to keep your inbox clean, and with most services that layers in the redundancy you’d have with a hosted solution, to prevent lost email if your server or internet connection goes down.

Our Own Email: What We’ve Done

Like many companies, we started with a basic POP account. As we grew, we used some Exchange features but moved to Google Apps as our primary solution. As we continued to grow, it lacked critical features we needed, including security, integration, and ability to easily manage email settings across the company. We moved back to Exchange, and it was absolutely the right solution for us. We are operating far more efficiently, and our software is completely integrated so we can schedule and communicate with our clients seamlessly from our ticketing system.

My favorite (and unexpected) benefit of our return to Exchange? The integration with my iPhone is superb, night and day from what it was with Google Apps. I no longer have to sync my phone because it pulls directly from our server. That means that if someone in the office adds an appointment to my calendar, it’s automatically there next time I check my phone. Email and contacts too.

Black, white, or shades of grey: the lists that control your email

In the email world, most anti-spam programs use lists as part of their effort to figure out who’s legit and who’s not. A blacklist is the worst and can affect your ability to send email to nearly anyone. A whitelist is maintained by a single person or company, but it says you are approved and can send email to them anytime. A greylist, no surprise, is somewhere in between.

Blacklists are managed by a variety of spam-prevention services. They flag people, websites, and servers that are known spammers. Many anti-spam programs rely on these lists to filter out bad email. If you are caught on one, you will undoubtedly have problems delivering your message. Since different email servers rely on different lists, you may find most email gets through and only a few people have problems. Get on a big enough list – or several lists – and the number of issues will increase.

Even the innocent get blacklisted. For example, a spammer may “spoof” your email, making it appear that you are a spammer even though messages come from a completely different source. If you start getting bounce-back messages as mentioned above, that make it appear you sent large batches of obscene or get-rich-quick emails to people you don’t know, that’s the most likely cause. There’s no way to prevent this; wait a couple of days and it will usually subside.

Another frequent problem arises because small businesses often share email servers via a hosted service. If someone else on your server is a spammer, everyone is in danger of being blacklisted. If this happens, you’ll start getting bounce-back messages with a spam-related error message.

Blacklist removal can be extremely simple or extremely complex – it all depends on the list, but blacklists assume you are guilty until proven innocent.

Greylists are less serious but can be equally frustrating because they are harder to track down. Many large organizations will use these to filter email from senders they haven’t seen before. As long as your message isn’t spam, this will more likely delay your message than completely block it. However, if you need quick response and the email doesn’t arrive for a full day, it creates a significant communications obstacle.

When the delay is a one-time occurrence and your next message gets through, there’s no need to do anything. Keep in mind you may encounter delays with several recipients; it’s only cause for concern if you run into multiple delays with the same person, or even the same company.

If your message never arrives, contact your recipient’s email administrator and request to be added to their whitelist. That’s their list of approved email addresses that always get through.